


The Intern

by LetsJustForget (WithallthisDelusion)



Category: Supernatural
Genre: Affairs, Age Difference, Alternate Universe - Celebrity, Alternate Universe - Office, Anal Fingering, Anal Sex, Bisexual Castiel (Supernatural), Blow Jobs, Cheating, Depression, Desk Sex, Domestic Violence, Drug Use, Explicit Sexual Content, Gay, Implied/Referenced Domestic Violence, Interns & Internships, Kissing, M/M, Older Castiel (Supernatural), One Shot, Oral Sex, Plot What Plot/Porn Without Plot, Strangers to Lovers, Swearing, Unhealthy Relationships, Window Sex, Young Dean Winchester, alternative universe
Language: English
Status: Completed
Published: 2020-03-19
Updated: 2020-03-19
Packaged: 2021-02-28 20:15:27
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 7,289
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23213116
Author URL: https://archiveofourown.org/users/WithallthisDelusion/pseuds/LetsJustForget
Summary: Dean's excited to start his internship at the largest advertising company in New York, only to find that it isn't what he expected.Perhaps it's even better as Dean finds himself working tirelessly to meet Castiel Novak's every demand.//Or the one where Naomi is a bitch to Castiel, and Dean is there to show him what a real relationship is meant to be like.
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester, Castiel/Naomi (Supernatural)
Kudos: 106





	The Intern

Tugging his backpack a little higher up over his shoulder, Dean Winchester shuffled his way inside the sky-high office building. He was instantly hit with a cold blast of air, experiencing a chill that he hadn’t felt since he was admitted to the hospital with a high fever as a child.

He sighed, enjoying the cool breeze. His room-share didn’t have air conditioning or windows that opened more than 3cms. It was a luxury that he missed since he moved out of his hometown and settled in the big apple.

Dean was in his second year at university, studying advertising. He was surprised that he didn’t fail last year, and instead he had managed to top the class. In recognition, the uni sent him off to an internship with one of the largest marketing companies in New York. He was terrified, mostly that he would make a fool of himself.

As he walked up to the reception desk, he suddenly felt out of place. Everyone surrounding him was wearing suits, or dresses or at least something that covered most of their skin. Dean somehow forgot that most offices didn’t approve of jeans and a t-shirt. He stared down at his ratty outfit, wishing he had something better at home. But he didn’t earn enough from bartending to splash out on fancy clothes.

“Why are you here?” The receptionist sneered, eyeing him skeptically.

Dean swallowed thickly, “I’m here for an internship, with Retrospective Media-“

“Are you shadowing Mr. Crowley or Mr. Novak?”

The young man blinked, “Uh… Not sure.”

She sighed, “Do you have your registration email?”

“Oh yeah!” Dean fumbled his phone out of his pocket, switching on the mobile data as he tried to load his most recent emails. “Is that the one from the staff portal or general inquiries?”

“Give it.” She mumbled, holding her hand out. He easily dropped it in her hand, as she flicked through his emails and finally found the right one. “Okay, you are shadowing Mr. Novak for three months.” She tapped on her computer, as a printer buzzed behind her. She returned his phone and reached behind her to collect a freshly printed pass. “Wear this at all times. Take the lift up to level 14 and speak to the receptionist there.”

Dean gave her a grin, “Thank you very much.” He slipped the pass over his neck. “I’ll see you this afternoon then.” She gave him an uncomfortable look, as he walked past.

He headed up in the elevator, fiddling nervously with the pass he was just given. It only had his name and his finish date printed on it, but it was still the coolest thing that he had.

Dean was uncomfortably squished in the lift with other businesspeople, their suits were neatly pressed, and it once again reminded him that he wasn’t dressed to impress. He vowed to himself that he would detour home via the shops and to buy some button-up shirts. More people left the lift the higher it got up and he was bursting with excitement once the lift finally reached his floor.

He stepped out, eyeing the office and the people sitting around it. He shuffled over towards the reception, smiling brightly at the young lady sitting behind the desk.

“Hello!” He greeted.

The lady eyed him cautiously, “Let me guess, you’re the intern?”

He nodded, lifting his pass to show her. She seemed a lot friendlier than the other receptionist, as she returned his smile. “Awesome to meet you, Dean! I’m Charlie, how about I introduce you to your attachment?”

He nodded enthusiastically as she guided him around the office, briefly pointing out the bathrooms, the staff kitchen, and the photocopy room. Dean still couldn’t believe he had scored this internship, it was going to do wonders for his resume. Yet, alone his wallet as it was offering him more money than his bartending job did. 

“So, Castiel Novak specialises in print media, so your posters and still image ads,” Charlie explained as they walked down a long corridor. “He used to be the executive product director, but…” Charlie suddenly stopped walking, spinning on her heels. “Rumour is that he keyed the CEO’s car and set fire to all their paperwork during a meeting.” She then casually started walking again, as Dean jogged to catch up. “But it’s just a rumour, he’s a lot more normal than you think.”

Dean blinked awkwardly, trying to wrap his head around what he just heard. He hoped this office wasn’t crazy, and not anything like something from the 'Devil Wears Prada'. Although it might be a little bit more fun. He quickly caught up to Charlie, as she swung a door open with a gold plaque titled ‘Castiel Novak.’

The intern followed Charlie in as they entered a waiting room, another door standing before them with another name plaque. Dean looked around the mini room, it was nicely decorated with pot plants and had an amazing view of the city below. The small space offering way more than you needed for a brief wait. “Hey Castiel, got your intern. I’ll leave him here, just give him a buzz when you’re ready.”

Charlie gave Dean another smile. “Sorry I gotta head back, he shouldn’t be too long. Come find me at lunch, and I’ll suggest some wicked places to eat at.”

“Sweet, thanks!” Dean replied, giving her another grin as she quickly slipped out of the room. The door slowly shut behind her, and soon Dean was left alone in the waiting room.

He wandered over to the window, staring down at the city below. He was still trying to figure out whether he would wish this internship to be over quickly, or whether it would be one that he would never want to leave. He couldn’t hide the smile over his lips, as he continued to count the traffic lights on the streets below. Either way, he was going to take the opportunity to enjoy the view.

Suddenly he was joined by a weird electronic buzzing sound. He flicked his eyes over towards the intercom, just as the sound cut out. He readjusted his bag, carefully walking over towards the door. He took in a deep breath, straightening his shoulders as he pushed on the door.

It peeled open slowly, as his eyes adjusted to a bright white office, balanced with grey and navy furniture. There were barely any walls, as big windows stared out at the bustling city instead. Dean crept inside, continuing to scan around the room. A few meters in front of him was a big glass desk, fitted with a computer and a slim stack of papers. He then heard a soft murmur, he followed the sound, as he looked towards a connecting room. Fitted with cupboards. It looked like a walk-in wardrobe from where he was. He crept closer, wondering where Mr. Novak was.

He heard the voice again, this time he could notice a hint of anger to it. Dean instantly felt uncomfortable. Especially as that deep heated voice had his skin tingling in a distracting way. “I said leave it!” They argued. Dean was frozen to the spot as he threw a glance back at the office door, wondering if he could make it back outside without making a sound. “Don’t be a bitch. You know that’s not what I meant!”

Dean took a step backward, figuring out that he hadn’t been buzzed in, it must have just been feedback from the system. The intern had managed to take a few steps before the man suddenly stepped out of the wardrobe, his head was down as he clutched his phone tightly in his fist. “Yeah, bigger is it?” He scoffed, “Well thanks for that wonderful insight Naomi, I hope it fits better in your massive cunt!”

Standing awkwardly by the door, Dean remained frozen. His boss hadn’t noticed him yet, as Mr. Novak continued to walk towards his desk. “Fuck you too!” He dropped himself down into his chair, sighing out. “I won’t.” He grunted, slamming his phone to the desk as he finally looked up.

Dean didn’t know where to look, or where to put his hands as he felt pinned by Mr. Novak’s gaze. He expected his boss to be embarrassed or something, but instead, he seemed impartial. “Who are you?” He asked, his dark blue eyes piercing the boy as the anger seemed to dissolve from him.

“I’m Dean Winchester, the intern.” He mumbled quietly.

Mr. Novak let his eyes rake over his body, “So that’s why you’re dressed like an intern.” He nodded in understanding. “Do you even own a suit?” It was just a question, but the way he said it, had Dean shuffling uncomfortably.

“Yeah, but it’s… back home.” Dean admitted, trying not to feel trashy in his favourite pair of jeans. He knew they looked good on him, they clung around his legs perfectly.

Mr. Novak frowned, “Why don’t you go home then, get a suit and then come back when you’re ready to dress like a man.”

Dean swallowed thickly, nodding. “Okay.” He mumbled, turning his back and swallowing his disappointment.

“Hold it.” Mr. Novak said, his voicing cutting through the silence. Dean turned back to face him, trying to hide the unease riddled across his face. “I need you to pick something up for me.” The man flicked through his computer, as Dean waited uncomfortably. Mr. Novak eventually found what he needed, as a robotic whirl sounded from the wardrobe. “Get that for me.”

The boy nodded softly, quickly walking over to get the paper. He entered the small space, his eyes drifting amongst the well-pressed suits and his large collection of ties. He then found the small printer resting on a shelf. He grabbed the piece of paper, glancing down at the contents. It had a photocopy of Mr. Novak’s driver’s license, he paused for a moment staring at his photo. It didn’t do justice to the jut of his jaw, or the strength in his eyes. Dean then quickly returned to his desk, handing over the piece of paper.

The man snatched the page, scribbling something underneath the photo. Dean stood by the desk, taking the opportunity to glance over his desk. He noticed a magazine off to the side, it looked like a thrashy mag that had a paparazzi pic on the front. It looked like an arguing couple, with the catching words ‘Market Clash?’. Dean leaned a little bit closer, eyeing the shirtless man on the front. He has broad shoulders, with a strike of dark hair.

Mr. Novak slammed his hand on top of the magazine, holding out the piece of paper. “Take this, you’ll need to go to the store opposite the building. They have my scripts on standby.” Get it on your way back.” He muttered, before pulling his wallet out. “Here.” He handed over his credit card.

“Oh, okay,” Dean mumbled, taking the offered items before stepping back. “Thank you for this opportunity, I’m really excited to be working with you.”

He was met with silence, as Mr. Novak began to type on his computer. Not giving the intern another minute of his time. 

Dean quickly left, slipping out of his office, and his waiting bay. He gave Charlie a mini-wave on his way to the lift before he finally let himself read what his boss had scribbled on the page.

‘ _I Castiel James Novak, authorise one Dan Winchester to pick up a single script of Citalopram_.’ It was signed and dated.

The intern blinked at it, suddenly feeling completely out of his depths. He instantly knew what the medicine was, and what it was used for. He felt his chest sink with each breath, as he tried to ignore the ebbing paranoia creeping into his thoughts.

He stepped out of the lift and continued out of the front doors. He knew it would be impossible to travel back to Kansa just to get the suit that he wore at his mother’s funeral. He wasn’t exactly keen to wear it ever again either.

He slipped down the street, feeling overcrowded by the people rushing past him. He set his targets on a nearby shopping center. But didn’t enter, instead he walked around to the back, where there was an op-shop. He finally settled on buying a navy-blue suit, that fit him well enough. 

He tossed his jeans and t-shirt in his backpack as he walked towards the chemist, constantly readjusting his new suit. It was a little too tight around the crotch area, but at least it clung perfectly around his thighs. He hoped that Mr. Novak would like the suit, it was meant for him anyway.

Dean slipped inside the chemist, buying Mr. Novak’s antidepressants on the credit card he was given. He then crossed the street and went up in the lift. He continued past Charlie, as he entered the waiting room again. He carefully buzzed for Mr. Novak this time, waiting until there was a click. “Hey, it’s uh… Dean.”

“Come in.” His boss’s deep voice grated.

The boy carefully pushed the door open, popping his head in and giving his boss a small smile. He then gestured down to his new suit. “Better?” He asked.

Mr. Novak’s eyes slipped down his body, his gaze falling heavily as it seemed to land on his crotch. “Much.” He agreed. His eyes quickly returning to the documents scattered over his desk.

Dean slipped his bag off his shoulder, pulling out his credit card, the scribbled piece of paper and the pack of Citalopram. “Here you go.” He placed them on the edge of his desk.

“Thanks.” He continued annotating the paper in front of him, as Dean shuffled awkwardly. “I have a meeting in a few minutes, and I need you to run through my emails and pick out all the resumes I’ve been sent.” He stood from the table. “I’ll be back before lunch.”

The boy nodded, excitement buzzing through him. “Okay sure.”

Mr. Novak snatched the box of medicine, popping one in his mouth and swallowing it dry. “If you have any troubles, give Charlie a call, she’ll help you out.” He quickly spun out of his office, slipping his suit jacket over his shoulders and disappearing outside.

Dean took the opportunity to flick over the documents on his boss’s desk, snooping over the budget sheets, and new design styles. He found a vibrant blue piece of paper, that had a shimmering silver design. It seemed to be a draft drawing of a new logo for a bottle of wine. It had sharp lines, that revealed a cityscape. It looked kinda boring to Dean, and he found himself tapping his fingers on the desk in thought. He picked up a scrap of paper and a pen.

He let his hand rest on the page, before he drew a swirl, crossing it over with another line as he chased the ink like a wave crashing to the shore. He shaded in a few lines, giving the presence of a light source.

He sat back staring at the new sketch, he easily preferred it over the other one. It had the right vibe for wine, as it was associated with waves of flavour. He sat the pen aside, as his finger bumped the magazine from earlier. He curiously picked it up, looking at the cover again.

Up close he could see more detail of the couple, the man was indeed very muscular and had incredible arms. His eyes flicked up towards his face, catching sight of the familiar sharp jaw and piercing blue eyes. It was him. Mr. Novak. On the front cover of a trashy magazine.

Dean instantly flicked through the magazine, reading the article and snooping over his boss’s messy break up with a long-term girlfriend and famous actor Naomi Carter. The photographs were incredibly invasive, catching Naomi slapping Castiel across the face, as he stood shirtless in their backyard. He read the gossip and started to feel sorry Castiel. It appeared that Naomi had cheated on him with many other guys, as Castiel was kicked out of their place.

No wondered he needed antidepressants after that, Dean sighed, closing up the magazine and putting it back to where it was before. It gave extra meaning to the fight Mr. Novak was having on the phone when he first walked in. He couldn’t understand how Naomi could be that cruel to him.

Dean looked over to the computer, figuring that he should probably start doing the research task now.

-

Mr. Novak wasn’t back before lunch, and instead, Charlie had to drag Dean out of the office to finally get him to eat. She introduced him to a neat little sandwich shop, that served amazing food for decent prices. She even detoured with him to a hipster coffee place that served the best cuppa he had ever had.

Soon Dean was creeping back into Mr. Novak’s office, but when he opened the second door, he found his boss sitting at his desk staring down at the scribble Dean had made earlier.

“Did you draw this?” Mr. Novak asked, lifting his head with a frown on his face.

The intern shrunk, fiddling with his new suit as he looked away. Feeling stupid that he had forgotten about his little scribble. “Uh yeah, sorry.” He mumbled.

Mr. Novak continued to start at the drawing before he made an affirmative sound. “I like it.” He lifted his head, as they met each other’s eyes. “That list of resumes I wanted you to compile was to help me find an artist to draw the new cover art.” He looked back at the scribbled paper, “But I like this.” Then he smiled at Dean.

A smile.

Dean was frozen, half in disbelief and the other half in awe at how beautiful his dimples were. He soon found himself smiling along, as a blush crept over his cheeks. “Thanks, Mr. Novak.”

“Please, just call me Castiel.”

-

A few weeks into the internship and Castiel had contracted Dean to draw three new logos. For the first time, Dean had felt encouraged and proud of his drawings, he hadn’t taken it seriously before but suddenly found himself with hundreds of new ideas for tattoo art, wallpapers and more logos.

Things had gotten better between Dean and Castiel too, sometimes they would chat about different types of colour schemes or their favourite cheesy ad from the 80s. But other times Mr. Novak would shut down completely, he would spend most of the day leering over his phone, sometimes getting calls that Dean knew were from his ex-girlfriend.

Dean didn’t want to get too attached to the people at his internship, especially as his last few days were approaching but he couldn’t help worrying for Mr. Novak. He was a very smart and creative guy, with so much to offer. Sure, he could be a real arse a lot of the time, but so could everyone.

Dean was leaning over Mr. Novak’s desk, as they were both trying to stare at the same thing on Mr. Novak’s computer. It had been one of Mr. Novak’s bad days, as he remained passively silent. Letting Dean draw for most of the day. “Could you make this colour a bit catchier?” Mr. Novak asked, flicking over Dean’s draft poster.

Suddenly there was a buzz from the intercom, and Castiel sat up, accidentally bumping Dean’s shoulder.

 _'Mr. Novak, uh… you have a visitor. It wasn’t scheduled…’_ Charlie’s nervous voice crackled through the speaker.

“Who?” Mr. Novak asked.

 _‘It’s your girlfriend… sir.’_ Charlie mumbled.

Dean could see the very moment when Mr. Novak tensed completely, he was suddenly sitting stiffly as his fists clenched together. “Fine, send her in.” He accepted, taking in a deep breath before lifting himself to his feet.

They both prepared for the disaster that was going to happen. Dean worrying that they might have gotten back together, considering Charlie referred to her as his ‘girlfriend’. Or unless he had a new girlfriend, he wondered. The intern stood awkwardly by the window, whereas Castiel stood by the desk hoping that his shoulders weren’t shaking each time he drew in a breath. There were only so many times he could be broken down before he would just finally cave in and let all the emotions kill him.

The door burst open as Naomi strutted in, the air around her filled with elegance as her eyes narrowed on her partner’s. “Why do you make it nearly impossible for me to see you?” She started, finally taking in the sight of the awkward intern by the window. She frowned at him, before deciding to just ignore him. “I’ve called three times this week to arrange an appointment, but your skanky receptionist refused to organise a date.” 

“I’ve been busy, Naomi.” Castiel stated, moving around to the front of the desk, leaning his hip against it and crossing his arms.

She scoffed, “That’s bullshit, you haven’t printed a single ad since you got de-promoted to babysitting.” She spat, throwing a finger towards Dean.

“Hey!” Dean grumbled, taking a step towards her.

Castiel threw the intern a warning glare, “Look, Naomi, now isn’t a good time. I’m free sometime next week instead. But right now we’re working on something important. I have to ask you to leave.”

She huffed, marching towards him and pressing a polished finger against Castiel’s chest. “You will never ask me to leave.” She gritted between her teeth. “I still owe you Castiel. I made you!”

He shook his head, standing up to face her. “You haven’t given me anything but pain.”

She laughed, tossing her head back. “Don’t make me laugh, I can’t believe how pathetic you’ve become.” She threw a glance towards the young intern. “I used to remember when you would cancel all your meetings, and you would lock the door.” She trailed a finger up from his arm to his chest. “Just you and me.” She flicked her long lashes up to him, her tongue wetting her lower lip as her teeth sunk into the plump flesh. “How you would fuck me-“

“Fuck off… please.” Mr. Novak muttered.

She yanked her hand back, suddenly slapping Castiel across the cheek as his head whipped to the side.

Dean gasped, as he fought his feet from chasing over to see if he was okay.

“Don’t you dare speak to me like that.” She spat, suddenly spinning on her heels and disappearing out of the office.

Castiel’s shoulders dropped once she left, as he brought his hands up to cover his face.

Dean quickly moved to stand before his boss, gently placing a hand to his shoulder. “Hey, are you okay Castiel?”

Castiel breathed in deeply, lifting his head and dropping his hands. Dean took in the sight of his swollen cheek, bright red with a small cut over his cheekbone. “Shit, you’re bleeding.” Dean panicked, reaching out to lift Mr. Novak's head to see the large bruise forming.

“It’s nothing.” He muttered, pulling his head out of his grip. “I just wish she didn’t wear those fucking rings like knuckle dusters.”

Dean couldn’t help but chuckle at the thought, it made Castiel laugh too as the stinging pain slowly faded. “I’ll get you some ice.” Dean mumbled after a moment, slipping outside of the office and towards the staff cafeteria.

When he returned, he found Castiel slumped in his chair, with his shirt sleeves unbuttoned and rolled up to his elbows. The intern slipped behind his desk, and gently placed the bundle of ice cubes wrapped in a paper towel to his cheek. “Is it sore?” He wondered.

“It’s fine Dean,” Castiel mumbled. The intern lifted the ice away, staring at the small cut that had already stopped bleeding. “Sorry, you had to see that.” Mr. Novak murmured, raising his head to meet the boy's eyes.

Dean had a small frown in his brow as he continued to inspect the forming bruise, “I’m just worried about what she would have done if I wasn’t here.” Dean replied. Knowing that Naomi and violence had a history of going hand in hand.

Castiel sighed, reaching up and holding Dean’s wrist. “Besides this, she’s more bark than bite.” He instantly noticed Dean’s skyrocketing heart rate, as he felt the pulse underneath his fingertips.

“I just don’t like her treating you like that.” Dean breathed, swallowing nervously as he was distracted by the dark blue in his boss’s eyes. His jawline was scattered with fresh stubble, and his dry lips were parted. He looked impossibly inviting. Castiel hissed as Dean subconsciously pressed the ice pack harder against his cheek, “Shit sorry Cas.”

His boss chuckled, “Cas?” He wondered, “Never been called that before.”

The intern blushed, wetting his lips nervously as Cas’s eyes followed the movement. “Dunno, just thought it sounds a lot less formal than Castiel or Mr. Novak.”

Cas grinned, “I like it.”

Dean ducked his head, as he lifted the ice pack away, inspecting the slowly forming bruise. “It looks kinda swollen.”

Mr. Novak shrugged, “I’ll survive.”

“Wish it never happened in the first place.” Dean mumbled.

Cas stifled a laugh, “Since when you do care for me? Aren’t I just a mean and scary boss?”

“No, not at all! You’re sweet and friendly.” The boy shook his head, “I mean, at first you were scary, and when you’re stressed...” He admitted, tilting his head in thought. “And after you talk to Naomi.”

Castiel suddenly stood up, causing Dean to stumble backward, dropping the ice pack as Cas pushed him back against the long glass window. Dean found his hands pressing against Cas’s firm chest. Dean’s breath hitched as Cas invaded his space, and the air escaped them. Hoping his racing heart wouldn’t give away how nervous Dean was feeling, he cautiously shifted, accidentally feeling the scrap of Cas’s hips against his.

“Am I scary now?” Cas wondered with his deep voice.

The boy could feel the heat radiating from his skin, his scent was overwhelming, and the lack of distance between them was causing Dean’s blood to rush down south. “Yeah.” He breathed, his wide green eyes were flicking between Cas’s blue ones.

For a second Cas’s tongue peeked out, swiping over his bottom lip as Dean caught the distracting action. Once Dean started staring at his boss’s lips, he found it nearly impossible to look away. It felt so hypnotic, as Dean had his back to the world, it couldn’t care less about the drama, the media or the consequences for his actions. He was seriously tempted to tighten his hands in Cas’s shirt and drag him forward into a kiss. 

Cas chuckled, letting his hands slip away from the boy’s shoulders as he took a wobbly step backward. “Just messing with you kid.” He shrugged, acting like they both couldn’t feel each other’s interest.

Dean sighed, feeling his shoulder slouch as his lungs finally found oxygen again. He tried to force a smile on his face, but he couldn’t hide his obvious disappointment.

The boss moved back towards his desk, keeping his back to Dean as he tried to ignore the tightness in his pants, and the ache in his gut to pin the boy back down. He picked up some papers trying to distract himself with the pointless information and to try to get emerald green eyes out of his head.

“Sir?” Dean’s soft voice asked.

Grunting in acknowledgment, Dean carefully approached Castiel. Picking up the ice pack on his way, as he carefully placed it to the edge of the desk. “Did you have any more feedback for my poster?” He asked quietly.

Castiel swallowed thickly, easily falling back into his seat and loading up the computer. He nearly jolted when Dean brushed against his shoulder, as he leaned back in to stare at the screen. “No. Looks good.” Castiel suddenly stated, leaning back as Dean gave him a confused stare.

“But you’ve only seen the first page. There’s another.” Dean mumbled.

Castiel lifted his eyes to the boy, noticing a light blush against his cheeks. “It’s fine. I just… need to…” He didn’t know what he needed. Honestly, he needed a good fuck. Or maybe to call up his bitch of an ex-girlfriend and scream with her for a while.

“I understand.” Dean said sadly, biting his lip as he frowned at the computer. It had Castiel feeling disappointment for himself for carrying on like an arsehole. All of a sudden, Dean was leaning right across Castiel’s desk. Clicking on the keyboard and pulling out his USB.

Cas’s eyes looked over him, as he sighed deeply at the sight of the boy stretched over his desk. His blue eyes drifted across the defined muscles of Dean’s back, that moved underneath his tight shirt. His gaze continued to sneak over the boy’s arse, as he took in the firm muscle right before him. Making him wear a suit was the best decision of his life. “Dean.” Castiel breathed, tightening his hand against the handrails of his chair.

The intern leaned back, his shirt almost untucking from his stretch, as he gave Cas a bitter glare. The boss couldn’t hide the attraction from his features, his pupils were lust blown and his lips were parted. He gently placed a hand to Dean’s hips. “Was there something else you wanted to show me?” Cas asked, slipping his finger into the belt loop of Dean’s trousers and tugging him forward as the boy stumbled into his lap.

Dean gasped, his hands resting on Castiel’s shoulders as his boss’s hands circled his waist, holding him close to his chest. “I guess…” He murmured, his wide green eyes taking in Castiel’s features.

Castiel moved a hand in between them, gently flicking the button holding Dean’s pants up as he leaned forward. “Well, I’m all yours.” Cas stated.

Dean’s heart was racing, he could barely think straight as his body moved so easily over Castiel’s. His legs were parted as he kneeled on the chair, feeling his boss’s muscular thighs underneath him. He was completely distracted by the sudden change, that he didn’t know where to put his attention first. Instead, he just stumbled over, cupping Castiel’s jaw and pushing their lips together. 

The gentle slid of Dean’s lips, confused Castiel at first. He hadn’t been kissed like this for years. He almost forgot how to tease his tongue over the boy’s lower lip to deepen their kiss. He could feel Dean’s fingers thread through his hair, tugging his head back as he chased his tongue with his own.

Moaning into the kiss, Castiel continued to unclasp Dean’s trousers as his fingers moved to the zipper. He could feel Dean shaking in his arms, the boy was so nervous. It squeezed Cas’s heart with a sense of fondness.

Dean leaned back, staring wide-eyed at his boss, complete panic drenching his features. Leaning forward, Castiel moved his hands to Dean’s hips. He suddenly stood up, holding Dean upright against his chest. Dean stared into Castiel’s eyes feeling his heart slamming against his ribcage. His body felt so hot, everywhere where Cas was touching him.

Castiel sent Dean a cheeky grin, before swiping half his desk onto the floor, scattering a pile of papers. Dean suddenly felt the cool edge of the glass desk against his thighs as Cas slowly laid him down against it.

Cas watched Dean’s puffing chest, as the boy withered against the desk. His entire body laid out before him. Castiel leaned over Dean, reaching his lips as he drew him back into a deep kiss. Cas ran his hands down Dean’s chest, feeling the hard muscles underneath his skin, his hand continued to explore over the boy’s body.

Dean had his hands tightening in Cas’s shirt, tugging him closer as he chased his lips. Dean couldn’t stop wiggling, as he felt Castiel’s hand trailing down his stomach. He whined softly, his hips suddenly thrusting up as he felt Cas’s hand slip underneath the waistband of his trousers.

Castiel pulled back from the kiss, chuckling deeply as he looked over the boy’s face. He could see a blush sneak up Dean’s neck as he looked away. “You’re beautiful.” Cas whispered, finally drawing Dean’s green eyes back to his, as the boy’s blush finally reached his freckled cheeks. Cas leaned back, moving his way down along Dean’s body.

“What are you-?” Dean wondered as Cas settled himself between Dean’s parted legs, his hands pulling down Dean’s trousers. “Oh.”

He wasn’t able to hide his smirk, as Castiel bared Dean’s cock. He heard Dean’s head thumping back against the desk, as Castiel wrapped his hand around it.

It had been years since Castiel had touched someone else’s cock, since he university days when he was exploring. He never did decide his sexuality, but he knew at this point that he didn’t want anything else, but Dean laid bared on his desk and his firm cock in his mouth.

Cas started stroking Dean’s dick, sending the boy into another wave of withering as he moaned softly. Cas focused on loosening his grip along his shaft and tightening his hold around the head. Dean thrust into his hand, as his lips parted as he heaved in air.

Leaning forward, Cas drew his tongue along the boy’s dick, softly tracing the underside of his cockhead. He followed this up by taking his entire cock into his mouth, bobbing his head and sucking firmly.

“Uh fuck.” Dean gasped, banging his head back against the desk.

Castiel continued fucking his mouth on the boy’s cock, licking up his cock before he pulled away with a pop. Staring with pride at Dean's hard cock. He flicked his eyes back up to the boy as Dean remained tensed, as he leaned up trying to calm his racing heart.

Standing up, Castiel tugged the rest of Dean’s pants off. He stared down at the boy, reaching underneath the desk as he opened a drawer and pulled out something that Dean couldn’t see. The intern was staring at his boss, trying to push words out of his mouth, but he could get his tongue to move. He was still trying to understand that his boss had his cock in his mouth only a moment ago. He was too busy trying to reconnect his brain to his mouth that he yelped when he suddenly felt the cool slid of lubricated fingers reaching between his legs.

Castiel had a grin over his lips, as he spread Dean’s thigh, gently sliding his fingers into his arse. “Cas.” Dean whined, Castiel flicked his eyes back up towards the boy as he was returned with Dean's nervous eyes, and with his teeth sunk into his bottom lip.

“Yeah?” Cas asked, gently stretching Dean’s hole.

“I haven’t… I can’t-”

“Oh, it's fine.”

Castiel quickly and carefully removed his fingers from Dean, wiping the lube on his trousers. He sighed, running his fingers through his dark hair. And trying to control his racing thoughts. Castiel took a few steps back, leaving the half-naked boy, with the hard cock on his desk as he tried to ignore his own throbbing erection.

Dean sat up on the desk, watching Cas walking away. He could feel his hard cock bumping against his stomach and he knew it wasn't just going to go away. He would have to deal with it before attempting to pull any type of pants over it. “I didn’t mean to…” Dean mumbled.

“Then what’s the problem?” Cas muttered over his shoulder as he continued to walk towards the window.

Wringing his wrists nervously, Dean shuffled off the desk. “I haven't ever been the one to...”

Castiel remained with his back to the boy, running a stressed hand down his face. He shouldn’t have tried anything, it was a mistake. Cas tried to ignore the gnawing shame in his gut as the doubt worked wonderfully to kill his hard-on. This was his problem, he could never learn what people wanted, not even with Naomi. He just always made a fool of himself, and now he ruined whatever he had going on with Dean. He was probably going to lose his job and be convicted with assault.

Feeling a sudden pressure against his shoulder, Castiel jumped, spinning around to see a nervous Dean standing behind him. “I’m sorry,” Dean mumbled, his eyes looking oddly determined. “I didn’t want you to stop. I just… don’t know what to do. But I want you to do it.”

Castiel shook his head, “I don’t think this is a good idea.” 

Frowning, Dean stepped closer, grazing his chest against Cas’s. He kept peering up into his eyes, as he gently placed his hand against his boss’s chest. He could feel the rapid thump of his heartbeat through his shirt.

Castiel’s fingertips were tingling, trying to fight the urge to reach out and kiss the boy. Dean decided for him though as he lifted himself on his toes, pressing a kiss to his lips.

Cas couldn’t fight it anymore, as he wrapped his arms around Dean’s waist, hauling him against his body. They gently slid their lips together.

Cas suddenly shoved Dean against the window, slipping his knee in between Dean’s legs, gently grinding his thigh against Dean’s balls. The boy whined softly, as Castiel gently pressed a finger against Dean’s entrance again.

This time Dean remained quiet as Cas gently stretched him open. Dean’s head rolled back against the glass window as he felt Cas’s lips pepper light kisses over his throat. Castiel pulled his fingers away, as he gently spun Dean around as the boy pressed his palms against the glass.

Castiel unzipped his trousers, tugging his pants down as he lined his hard cock at Dean’s entrance. Cas smoothed a hand over the boy’s shoulders, scratching his teeth over Dean’s neck. He gently pushed inside the boy, moaning as he was engulfed by warmth. “Fuck Dean.” He grunted, settling himself inside, waiting until Dean’s tensed shoulders relaxed. “I’ve got you, come on baby.” He murmured, circling a hand around Dean’s waist and taking his still hard cock in his hand. He began to slowly stroke him, as he pulled his hips back, matching their rhythms together.

Dean groaned loudly, dropping his head against the glass as he relaxed into Castiel’s hold.

The wide window showed the city below, and it had Dean’s skin tingling with awe at how much Castiel was willing to risk by showing him off to the city below.

Castiel thrust deep inside his intern, feeling his breath rush out unevenly. “Christ.” Cas gasped, as Dean pushed his palms against the glass and met each of his thrusts. Against the bright city sky, Dean let his eyes fall shut as he soaked in the feeling of Castiel’s warm body situated behind him.

His fingers gently tightened over Dean’s cock, drawing him closer towards his orgasm as Castiel focused on the soft hitch in Dean’s breath. Cas hadn’t held someone like this for so long. He had forgotten how good it felt to have someone wrapped up in your arms. To feel his heart beating against his own.

Dean groaned, his hips moving back wildly as he lost his rhythm, just seeking out the pleasure Castiel was providing him. Hiding his chuckle Cas slowed down his movements, removing his hand from Dean’s cock as he slipped his hand underneath his shirt instead, reaching up to pinch his nipple.

“Oi!” Dean gasped, twisting his head over his shoulder to shoot Cas a glare. Castiel had stopped moving entirely, pausing to get better control over his building orgasm, before he pulled out completely. “What are you-“

Cas spun Dean around again, shoving his back against the window again as Dean was silenced by the heavy look in his boss’s dark blue eyes. Cas wet his lower lip, taking in the pink blush scattered over Dean’s faintly freckled cheeks. Castiel’s eyes continued down Dean’s body, as his fingers quickly moved to unbutton his crinkled shirt. He fought with the buttons, wresting the shirt off his shoulders as his hands gently smoothed over the intern's bare chest.

Dean’s breath stuttered as he felt Cas’s eyes linger over his crotch, his hands soon followed his eyes as he took hold of Dean’s erection. He gently stroked him, as he pressed a kiss to his shoulder. His other hand sneaked behind Dean as he gripped his arse for a second, before ducking down to grab the back of his thigh and hiking his leg up over Cas’s hip. Leaving Dean precariously open.

Heat instantly rushed down to Dean’s cock, as he felt Castiel’s own nudge gently at his entrance. “Ever been fucked like this?” Cas asked, moving a hand up to cup Dean’s jaw as he pulled their lips into a deep kiss.

Whilst dragging his tongue inside the intern’s mouth, Cas paired it with the slow push of his cock. Dean broke the kiss with the need to breathe as he moaned loudly, whilst Castiel’s cock slid inside him, pleasuring him from a different angle. Overwhelming the boy with all new kinds of sensations. “God no.” Dean answered, screwing his eyes shut as Castiel settled inside him completely.

Castiel tangled a hand in Dean’s hair, tilting his head forward as he returned their lips, dragging his hips back before slamming them forward. Each thrust causing Dean to release a sharp huff of air, as he shook in his arms, his orgasm creeping up quickly.

Finding Dean’s erection standing proudly in between them, Castiel wrapped his hand around it, giving him short and fast strokes. Dean moaned out between his clenched teeth as he felt his balls tighten for release.

With a final tug on Dean’s firm cock, the intern came between them coating his bare stomach and Cas’s crisp business shirt in his cum. Castiel chuckled, chasing Dean’s lips as he kissed him, only needing a few more thrusts inside the boy before he spilled inside Dean.

With their racing hearts and stuttered breathing, they remained embraced. Breathing in each other’s air and taking in the numbing pleasure between them. Dean let his head roll back against the window, as Castiel licked soft kisses over his shoulder.

After a silent moment, Dean lowered his leg from Cas’s hip as his boss removed his cock from his arse. Dean looked embarrassed as he kept his eyes glued to the polished floor. “What?” Cas asked, dragging his hand over Dean’s chest, and wiping up his cum.

Dean bit his lip, as he flicked his nervous eyes over to Cas’s. “What are we gonna do now?” Dean wondered.

Castiel continued to stare at the boy long after he spoke, he had the answer on the tip of his tongue, but he was too busy to think of where he wanted to put his tongue instead of saying anything. Instead, he stood beside his intern, causing him more stress and agony whilst he took in the cute sight of him. Cas finally figured out where he was going to put his tongue, as he sunk to his knees, licking a long stripe up Dean's stomach, tasting his bitter cum. Dean’s hands didn’t seem nervous, as they instantly thread through Cas’s dark hair.

All of a sudden the office door opened, “Oh… shit.”

Dean’s wide eyes instantly met Charlie’s as she stood uncomfortably by the door. Her eyes were almost as wide as his. After Castiel finished licking Dean clean, he stood up and sent a Dean a cheeky wink. Before spinning and greeting Charlie like nothing had happened.


End file.
